Rational design and immunogenicity of liposome-based diepitope constructs: Application to synthetic oligosaccharides mimicking the Shigella flexneri 2a O-antigen

Vaccine

Volumn 27, Issue 39, 2009, Pages 5419-5426

  Hassane, Fatouma Said ^a   Phalipon, Armelle ^b   Tanguy, Myriam ^b   Guerreiro, Catherine ^c   Bélot, Frédéric ^c   Frisch, Benoît ^a   Mulard, Laurence A ^c   Schuber, Francis ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b INSTITUT PASTEUR   (France)

^c CNRS   (France)

Author keywords

Liposomes; Shigella flexneri 2a O antigen; Synthetic oligosaccharide based vaccination construct

Indexed keywords

B CELL EPITOPE; EPITOPE; HEMAGGLUTININ; HEMAGGLUTININ PEPTIDE HA 307-319; LIPOPEPTIDE; LIPOSOME; O ANTIGEN; OLIGOSACCHARIDE; TOLL LIKE RECEPTOR 2 LIGAND; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIBODY RESPONSE; ARTICLE; CONTROLLED STUDY; DRUG CONJUGATION; DRUG DESIGN; DRUG SYNTHESIS; IMMUNOGENICITY; LIPOSOMAL DELIVERY; MOUSE; NONHUMAN; PRIORITY JOURNAL; SHIGELLA FLEXNERI;

ANIMALS; ANTIBODIES, BACTERIAL; BACTERIAL VACCINES; DYSENTERY, BACILLARY; EPITOPES, B-LYMPHOCYTE; EPITOPES, T-LYMPHOCYTE; FEMALE; HEMAGGLUTININS; LIPOPEPTIDES; LIPOSOMES; MICE; MICE, INBRED BALB C; MOLECULAR STRUCTURE; O ANTIGENS; OLIGOSACCHARIDES; ORTHOMYXOVIRIDAE; SHIGELLA FLEXNERI; VACCINES, SYNTHETIC;

EID: 68349101982     PISSN: 0264410X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.vaccine.2009.06.031     Document Type: Article

References (55)

1. Kelly D.F., Moxon E.R., and Pollard A.J. Haemophilus influenzae type b conjugate vaccines. Immunology 113 2 (2004) 163-174
2. Rappuoli R. Conjugates and reverse vaccinology to eliminate bacterial meningitis. Vaccine 19 17-19 (2001) 2319-2322
3. Pozsgay V. Recent developments in synthetic oligosaccharide-based bacterial vaccines. Curr Top Med Chem 8 2 (2008) 126-140
4. Verez-Bencomo V., Fernandez-Santana V., Hardy E., Toledo M.E., Rodriguez M.C., Heynngnezz L., et al. A synthetic conjugate polysaccharide vaccine against Haemophilus influenzae type b. Science 305 5683 (2004) 522-525
5. Schutze M.P., Leclerc C., Jolivet M., Audibert F., and Chedid L. Carrier-induced epitopic suppression, a major issue for future synthetic vaccines. J Immunol 135 4 (1985) 2319-2322
6. Baraldo K., Mori E., Bartoloni A., Norelli F., Grandi G., Rappuoli R., et al. Combined conjugate vaccines: enhanced immunogenicity with the N19 polyepitope as a carrier protein. Infect Immun 73 9 (2005) 5835-5841
7. Shahiwala A., Vyas T.K., and Amiji M.M. Nanocarriers for systemic and mucosal vaccine delivery. Recent Pat Drug Deliv Formul 1 1 (2007) 1-9
8. Alving C.R. Liposomes as carriers of antigens and adjuvants. J Immunol Methods 140 1 (1991) 1-13
9. Gregoriadis G. Engineering liposomes for drug delivery: progress and problems. Trends Biotechnol 13 12 (1995) 527-537
10. Fernandes I., Frisch B., Muller S., and Schuber F. Synthetic lipopeptides incorporated in liposomes: in vitro stimulation of the proliferation of murine splenocytes and in vivo induction of an immune response against a peptide antigen. Mol Immunol 34 8-9 (1997) 569-576
11. Friede M., Muller S., Briand J.P., Van Regenmortel M.H., and Schuber F. Induction of immune response against a short synthetic peptide antigen coupled to small neutral liposomes containing monophosphoryl lipid A. Mol Immunol 30 6 (1993) 539-547
12. Roth A., Espuelas S., Thumann C., Frisch B., and Schuber F. Synthesis of thiol-reactive lipopeptide adjuvants. Incorporation into liposomes and study of their mitogenic effect on mouse splenocytes. Bioconjug Chem 15 3 (2004) 541-553
13. Fortin A., Lagace J., and Therien H.M. Trafficking of surface-linked and encapsulated liposomal antigens in macrophages: an immunocytochemical study. J Histochem Cytochem 49 11 (2001) 1407-1420
14. Nair S., Buiting A.M., Rouse R.J., Van Rooijen N., Huang L., and Rouse B.T. Role of macrophages and dendritic cells in primary cytotoxic T lymphocyte responses. Int Immunol 7 4 (1995) 679-688
15. Grivel J.C., Crook K., and Leserman L. Endocytosis and presentation of liposome-associated antigens by B cells. Immunomethods 4 3 (1994) 223-228
16. Puffer E.B., Pontrello J.K., Hollenbeck J.J., Kink J.A., and Kiessling L.L. Activating B cell signaling with defined multivalent ligands. ACS Chem Biol 2 4 (2007) 252-262
17. Boeckler C., Dautel D., Schelte P., Frisch B., Wachsmann D., Klein J.P., et al. Design of highly immunogenic liposomal constructs combining structurally independent B cell and T helper cell peptide epitopes. Eur J Immunol 29 7 (1999) 2297-2308
18. Roth A., Rohrbach F., Weth R., Frisch B., Schuber F., and Wels W.S. Induction of effective and antigen-specific antitumour immunity by a liposomal ErbB2/HER2 peptide-based vaccination construct. Br J Cancer 92 8 (2005) 1421-1429
19. Levine M.M., Kotloff K.L., Barry E.M., Pasetti M.F., and Sztein M.B. Clinical trials of Shigella vaccines: two steps forward and one step back on a long, hard road. Nat Rev Microbiol 5 7 (2007) 540-553
20. Passwell J.H., Harlev E., Ashkenazi S., Chu C., Miron D., Ramon R., et al. Safety and immunogenicity of improved Shigella O-specific polysaccharide-protein conjugate vaccines in adults in Israel. Infect Immun 69 3 (2001) 1351-1357
21. Fries L.F., Montemarano A.D., Mallett C.P., Taylor D.N., Hale T.L., and Lowell G.H. Safety and immunogenicity of a proteosome-Shigella flexneri 2a lipopolysaccharide vaccine administered intranasally to healthy adults. Infect Immun 69 7 (2001) 4545-4553
22. Wright K., Guerreiro C., Laurent I., Baleux F., and Mulard L.A. Preparation of synthetic glycoconjugates as potential vaccines against Shigella flexneri serotype 2a disease. Org Biomol Chem 2 10 (2004) 1518-1527
23. Belot F., Guerreiro C., Baleux F., and Mulard L.A. Synthesis of two linear PADRE conjugates bearing a deca- or pentadecasaccharide B epitope as potential synthetic vaccines against Shigella flexneri serotype 2a infection. Chemistry 11 5 (2005) 1625-1635
24. Phalipon A., Costachel C., Grandjean C., Thuizat A., Guerreiro C., Tanguy M., et al. Characterization of functional oligosaccharide mimics of the Shigella flexneri serotype 2a O-antigen: implications for the development of a chemically defined glycoconjugate vaccine. J Immunol 176 3 (2006) 1686-1694
25. Vulliez-Le Normand B., Saul F.A., Phalipon A., Belot F., Guerreiro C., Mulard L.A., et al. Structures of synthetic O-antigen fragments from serotype 2a Shigella flexneri in complex with a protective monoclonal antibody. Proc Natl Acad Sci USA 105 29 (2008) 9976-9981
26. Phalipon A., Tanguy M., Grandjean C., Guerreiro C., Belot F., Cohen D., et al. A synthetic carbohydrate-protein conjugate vaccine candidate against Shigella flexneri 2a infection. J Immunol 182 4 (2009) 2241-2247
27. O'Sullivan D., Arrhenius T., Sidney J., Del Guercio M.F., Albertson M., Wall M., et al. On the interaction of promiscuous antigenic peptides with different DR alleles. Identification of common structural motifs. J Immunol 147 8 (1991) 2663-2669
28. Baraldo K., Mori E., Bartoloni A., Petracca R., Giannozzi A., Norelli F., et al. N19 polyepitope as a carrier for enhanced immunogenicity and protective efficacy of meningococcal conjugate vaccines. Infect Immun 72 8 (2004) 4884-4887
29. Reitermann A., Metzger J., Wiesmuller K.H., Jung G., and Bessler W.G. Lipopeptide derivatives of bacterial lipoprotein constitute potent immune adjuvants combined with or covalently coupled to antigen or hapten. Biol Chem Hoppe Seyler 370 4 (1989) 343-352
30. Takeuchi O., Sato S., Horiuchi T., Hoshino K., Takeda K., Dong Z., et al. Cutting edge: role of Toll-like receptor 1 in mediating immune response to microbial lipoproteins. J Immunol 169 1 (2002) 10-14
31. Deiters U., Barsig J., Tawil B., and Muhlradt P.F. The macrophage-activating lipopeptide-2 accelerates wound healing in diabetic mice. Exp Dermatol 13 12 (2004) 731-739
32. Said Hassane F., Frisch B., and Schuber F. Targeted liposomes: convenient coupling of ligands to preformed vesicles using "click chemistry". Bioconjug Chem 17 3 (2006) 849-854
33. Bohlen P., Stein S., Dairman W., and Udenfriend S. Fluorometric assay of proteins in the nanogram range. Arch Biochem Biophys 155 1 (1973) 213-220
34. Kaufmann S.H. The contribution of immunology to the rational design of novel antibacterial vaccines. Nat Rev Microbiol 5 7 (2007) 491-504
35. Altin J.G., and Parish C.R. Liposomal vaccines-targeting the delivery of antigen. Methods 40 1 (2006) 39-52
36. Schelte P., Boeckler C., Frisch B., and Schuber F. Differential reactivity of maleimide and bromoacetyl functions with thiols: application to the preparation of liposomal diepitope constructs. Bioconjug Chem 11 1 (2000) 118-123
37. Wiesmuller K.H., Fleckenstein B., and Jung G. Peptide vaccines and peptide libraries. Biol Chem 382 4 (2001) 571-579
38. Nardin E.H., Calvo-Calle J.M., Oliveira G.A., Nussenzweig R.S., Schneider M., Tiercy J.M., et al. A totally synthetic polyoxime malaria vaccine containing Plasmodium falciparum B cell and universal T cell epitopes elicits immune responses in volunteers of diverse HLA types. J Immunol 166 1 (2001) 481-489
39. Mittenbuhler K., v d Esche U., Heinevetter L., Bessler W.G., and Huber M. Lipopeptides: adjuvanticity in conventional and genetic immunization. FEMS Immunol Med Microbiol 37 2-3 (2003) 193-200
40. Buskas Ter., Ingale S., and Boons G.J. Towards a fully synthetic carbohydrate-based anticancer vaccine: synthesis and immunological evaluation of a lipidated glycopeptide containing the tumor-associated tn antigen. Angew Chem Int Ed Engl 44 37 (2005) 5985-5988
41. Ingale S., Wolfert M.A., Gaekwad J., Buskas T., and Boons G.J. Robust immune responses elicited by a fully synthetic three-component vaccine. Nat Chem Biol 3 10 (2007) 663-667
42. Ingale S., Wolfert M.A., Buskas T., and Boons G.J. Increasing the antigenicity of synthetic tumor-associated carbohydrate antigens by targeting Toll-like receptors. ChemBioChem 10 3 (2009) 455-463
43. Toyokuni T., Hakomori S., and Singhal A.K. Synthetic carbohydrate vaccines: synthesis and immunogenicity of Tn antigen conjugates. Bioorg Med Chem 2 11 (1994) 1119-1132
44. Toyokuni T., Dean B., Cai S., Boivin D., Hakomori S., and Singhal A.K. Synthetic vaccines: Synthesis of a dimeric Tn antigen-lipopeptide conjugate that elicits immune responses against Tn-expressing glycoproteins. J Am Chem Soc 116 (1994) 395-396
45. Reichel F., Ashton P.R., and Boons G.J. Synthetic carbohydrate-based vaccines: synthesis of an l-glycero-d-manno-heptose antigen-T-epitope-lipopeptide conjugate. Chem Commun (1997) 2087-2088
46. Bundle D.R. A carbohydrate vaccine exceeds the sum of its parts. Nat Chem Biol 3 10 (2007) 605-606
47. Shahum E., and Therien H.M. Liposomal adjuvanticity: effect of encapsulation and surface-linkage on antibody production and proliferative response. Int J Immunopharmacol 17 1 (1995) 9-20
48. Therien H.M., Lair D., and Shahum E. Liposomal vaccine: influence of antigen association on the kinetics of the humoral response. Vaccine 8 6 (1990) 558-562
49. BenMohamed L., Wechsler S.L., and Nesburn A.B. Lipopeptide vaccines-yesterday, today, and tomorrow. Lancet Infect Dis 2 7 (2002) 425-431
50. Snippe H., van Dam J.E., van Houte A.J., Willers J.M., Kamerling J.P., and Vliegenthart J.F. Preparation of a semisynthetic vaccine to Streptococcus pneumoniae type 3. Infect Immun 42 2 (1983) 842-844
51. Zigterman G, Verheul A, Snippe H. Liposomes as immunadjuvants for saccharide antigens. Liposome in Drug Delivery by G Gregoriadis. In: Florence AT, Patel HM, editors. Chur, Switzerland: Harwood Academic Publisher; 1993.
52. Robin G., Cohen D., Orr N., Markus I., Slepon R., Ashkenazi S., et al. Characterization and quantitative analysis of serum IgG class and subclass response to Shigella sonnei and Shigella flexneri 2a lipopolysaccharide following natural Shigella infection. J Infect Dis 175 5 (1997) 1128-1133
53. Robin G., Keisari Y., Slepon R., Ashkenazi S., and Cohen D. Quantitative analysis of IgG class and subclass and IgA serum response to Shigella sonnei and Shigella flexneri 2a polysaccharides following vaccination with Shigella conjugate vaccines. Vaccine 17 23-24 (1999) 3109-3115
54. Slack J., Der-Balian G.P., Nahm M., and Davie J.M. Subclass restriction of murine antibodies. II. The IgG plaque-forming cell response to thymus-independent type 1 and type 2 antigens in normal mice and mice expressing an X-linked immunodeficiency. J Exp Med 151 4 (1980) 853-862
55. Stein K.E. Thymus-independent and thymus-dependent responses to polysaccharide antigens. J Infect Dis 165 (1992) S49-S52